Palladium-Catalyzed Amination of Unprotected Halo-7-azaindoles
- 22 September 2010
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 12 (20), 4438-4441
- https://doi.org/10.1021/ol101928m
Abstract
Simple and efficient procedures for the Pd-catalyzed cross-coupling of primary and secondary amines with halo-7-azaindoles(pyrrolo[2,3-b]pyridine) are presented. Previously, no general method was available to ensure the highly selective reaction of the heteroaryl halide in the presence of the unprotected azaindole N-H. Using palladium precatalysts recently reported by our group, such reactions are easily accomplished under mild conditions that can be applied to cross-coupling reactions with a wide array of aliphatic and aromatic amines.Keywords
This publication has 13 references indexed in Scilit:
- Impact of Donor−Acceptor Geometry and Metal Chelation on Photophysical Properties and Applications of TriarylboranesAccounts of Chemical Research, 2009
- A Highly Active Catalyst for Pd-Catalyzed Amination Reactions: Cross-Coupling Reactions Using Aryl Mesylates and the Highly Selective Monoarylation of Primary Amines Using Aryl ChloridesJournal of the American Chemical Society, 2008
- A New Class of Easily Activated Palladium Precatalysts for Facile C−N Cross-Coupling Reactions and the Low Temperature Oxidative Addition of Aryl ChloridesJournal of the American Chemical Society, 2008
- Electronic Effects on the Selectivity of Pd‐Catalyzed C-N Bond‐Forming Reactions Using Biarylphosphine Ligands: The Competitive Roles of Amine Binding and AcidityAngewandte Chemie, 2007
- Synthesis and biological evaluation of 7-azaindole derivatives, synthetic cytokinin analoguesBioorganic & Medicinal Chemistry Letters, 2007
- Organometallic methods for the synthesis and functionalization of azaindolesChemical Society Reviews, 2007
- Analysis of the reactions used for the preparation of drug candidate moleculesOrganic & Biomolecular Chemistry, 2006
- Evidence for the Formation and Structure of Palladacycles during Pd‐Catalyzed C-N Bond Formation with Catalysts Derived from Bulky Monophosphinobiaryl LigandsAngewandte Chemie, 2006
- Efficient Pd-Catalyzed Amination of Heteroaryl HalidesOrganic Letters, 2005
- 3-[[4-(4-Chlorophenyl)piperazin-1-yl]methyl]-1H-pyrrolo[2,3-b]pyridine: An Antagonist with High Affinity and Selectivity for the Human Dopamine D4 ReceptorJournal of Medicinal Chemistry, 1996